Before we get into the meat of today’s post, take a moment to think about the last problem you took to your boss. Maybe it was a client who keeps moving the goalposts or a team member who’s stretched too thin or a deadline you knew wasn’t going to land.
When you walked out of that conversation, what did you want your boss to actually do?
If your honest (really honest) answer is “I’m not really sure” or “I just wanted them to know how I felt”, then you’re not alone. It’s what happens when you get promoted and it’s also the reason so many problems you’ve “raised” never seem to go anywhere.
We’re going to talk about the difference between venting a problem and escalating it. Venting gets it off your chest, whilst escalating gives your boss something they can actually act on. So let’s dive into why we get this wrong and what to do instead.
By the way – I’ve been in both positions here. The boss who is being vented at and the manager who is venting to their boss. I’ve seen both sides so I want to try and present a balanced view of how this situation happens and how to deal with it.
Why this is so hard (and why we get it wrong)
Before you were a manager, raising a problem was often simple. It was about the work: “This brief doesn’t make sense” or “I’m blocked on the data.” Your manager took it from there and helped you resolve the situation. Hopefully anyway!
Now you’re in the middle and your team’s problems land on you. Some of them you can solve whilst some you can’t, because they need a budget or a decision from above or someone senior to have a word with a client to get them onside with an idea. The person you need to take them to is also the person quietly judging how well you’re coping in the new role.
(Yes, your boss judges you on how you handle situations, not just the result or output).
That’s an uncomfortable combination for many of us. It pushes most new managers into one of two traps.
Trap one: the vent
You walk in carrying the frustration of the whole week or even the last few weeks. You explain the problem in detail and how annoying it is. Maybe you explain what everyone else should have done differently. Then the meeting ends.
It feels productive. To put it bluntly, it mostly makes you feel better. Your boss walks away knowing you’re frustrated, but with no idea what you need from them. So they do the reasonable thing: nothing.
Some bosses will understand that you’re just venting and that’s okay. Some won’t and will wonder what they should do. Worst case scenario, some bosses feel like you’ve wasted their time.
Trap two: the swallow
This is an overcorrection. You don’t want to look like you can’t handle the job, so you don’t raise it at all. You absorb it, work around it and tell yourself you’ll deal with it. Then it surfaces a few months later, bigger and harder to fix. Your boss’s first question is “Why didn’t you tell me?”
Both traps come from the same place. You haven’t decided what you want from your boss. So you either say everything or nothing.
What it looks like when it’s going wrong
Here are four signs you’re venting rather than escalating.
The status report
You give a detailed, accurate description of what’s happening, such as:
- The client is unhappy.
- The team is stretched.
- Timelines are slipping.
All accurate. But there’s no question attached, so it lands like a weather forecast: interesting, slightly worrying and nothing anyone can do about it.
The “just so you know” update
You flag things in passing at the end of a one-to-one or in a quick Slack message. You never push. When it eventually goes wrong, your only defence is “I did mention it.” Technically true, but not much help to anyone.
The repeating problem
You’ve raised the same issue in three different one-to-ones. Each time your boss nods, agrees it’s a problem and moves on. If the same problem keeps coming back with nothing changing, look at how you’re raising it before you decide your boss doesn’t care.
The leak
The frustration you didn’t put clearly to your boss comes out somewhere else. Usually in front of your team: a sigh in the team meeting, a “don’t get me started” or an eye-roll whenever leadership comes up. As we’ve spoken about before, remember that you’re always on stage. Your team picks this up far faster than you think.
How you can effectively take a problem upwards
1. Decide your ask or question before you walk in
This is the one that changes everything else. Before any conversation with your boss about a problem, decide which of these you need from them:
- A decision.
- Resource: time, budget or people.
- Air cover: support with a client, another team or someone more senior.
- Awareness only, because you’re handling it but they shouldn’t be surprised.
- Help thinking it through, because you don’t know the answer yet.
All five are legitimate asks of them and whilst some of them mean that you don’t already have an answer, you’re communicating that to them and asking for specific help.
Awareness on its own is fine too, as long as you say that’s what it is and what you’re doing about it. That’s the difference from the “just so you know”. The trouble starts when you (or them) don’t know which one you need.
Once you know, say it up front:
- “I need a decision from you on this by Thursday.”
- “I don’t need you to do anything yet. I want you to know before the client raises it with you.”
2. Lead with the business impact, not how it feels
Your frustration is real. But your boss can’t do much with it. What they can act on is what the problem is costing.
Compare these two versions of the same problem:
- “The client keeps changing the brief and the team is completely fed up.”
- “The client has changed the brief three times this month. We’ve lost time we can’t bill for and two people are working late to hold the deadline. If it carries on, we’ll miss the launch date.”
The second one gives your boss something to weigh up and decide on because it quantifies the impact of the problem.
3. Bring options, or say honestly that you don’t have them
As mentioned above, the common advice is to always bring solutions alongside your problems. I’m wary of that. A long time ago I wrote about why “bring me solutions, not problems” backfires when you say it to your team: people start sitting on the problems they can’t solve, so the hardest ones never reach you.
The same is true when you’re the one taking problems upwards. If you only escalate what you’ve already solved, the hardest problems never reach the person who could help.
So bring options when you have them:
“I can see two ways through this. We push the deadline by a week, or I move Sam off the other account for a fortnight. I’d go with the first. What do you think?”
When you don’t, say so plainly:
“I can see two options and I’m not convinced by either. Can we spend ten minutes thinking it through together in case I’m missing something.”
Both are fine. What doesn’t work is turning up with neither and no ask.
4. Use the four-line escalation
If you want something you can use every time, write these four lines before the conversation:
- What’s happening.
- Why it matters to the business.
- The options I can see (or that I don’t have any yet).
- What I need from you.
It takes less than five minutes. It forces you to work out your ask before you’re in the room. It also works as a message you send beforehand, so your boss turns up ready to decide rather than hearing it cold.
Before you leave, play it back: “So we’re agreed I’ll push the deadline and you’ll speak to the client on Monday?”
This helps ensure that you’re both clear on actions.
5. Label the vent
I’m not saying you should never vent to your boss. Sometimes you need to and it’s something that I used to encourage my team to do with me.
My logic was that everyone needs to vent sometimes and I’d rather they have a safe space to do it with me than with their team.
A bit of honesty about how the week has gone also helps them understand what’s going on with you.
The fix is to say what it is:
“I need two minutes to get this off my chest. Then I’ve got an actual ask.”
Your boss knows what’s coming. You get it out. Then you move on to the four lines. It’s a small thing, but it stops the vent from becoming the whole conversation.
*Sidenote: the same works in reverse. If someone on your team keeps bringing you status reports, ask them “What do you need from me on this?” It’s one of the most useful questions you can teach them to answer before they walk in.*
